While most visitors never make it past the Big Apple’s incredible array of world-famous attractions, the state of New York also has superb scenery, sights, and small towns to discover. Home to the soaring Adirondack Mountains and idyllic Finger Lakes, the state also lies next to the Atlantic, Lake Erie and Lake Ontario too—so it really does have several sides to it.
In the Empire State, you can find countless charming small towns to stay at, each with their own identity. While some are nestled amidst the mountains and offer outdoor activities, others are set along serene lakeshores and boast a wealth of historic sites.
Whether you’re after a relaxing weekend getaway, fun watersports or magical winter festivals, the small towns in New York certainly have something for everyone to enjoy.
Set at the northern end of the long and slender lake of the same name, Canandaigua is one of the most picture-perfect places to visit in the Finger Lakes region. Aptly meaning ‘The Chosen Spot’ in the local Native American language, it boasts immaculately manicured gardens, interesting historic sites and cultural landmarks.
The well-preserved historic center has magnificent mansions, monuments and a handful of fine museums. Aside from enjoying the lovely flower beds and gardens of its huge estates, you can also delve into the fine dining scene or try out wonderful wineries.
In addition, the lake offers all kinds of fun watersports and outdoor activities, while the lakeside Roseland Waterpark has slides, pools and a lazy river.
In contrast to sleepy, upmarket Canandaigua, the college town of New Paltz has a lively and youthful feel. Easily reached from both Albany and New York City, it lies in the southeast of the state, alongside Wallkill River.
As it was founded in 1678, the town has a rich history to explore with beautiful old buildings, bars and boutiques lining its streets. Besides countless cosy BnBs, the most memorable place to stay is undoubtedly Mohonk Mountain House. This is because the famous Victorian-era resort is set in a stunning spot, looks like a castle, and offers an array of amenities and attractions.
From New Paltz you can hike and bike around the incredible landscapes and nature of the Wallkill Valley, or venture up into the craggy mountains of the Shawangunk Range.
Although the world-famous music festival was actually held in nearby Bethel, the small town of Woodstock still attracts artists, musicians, free spirits and theater lovers. While it is most known for its thriving arts and culture scene, it is also located in an idyllic spot with mountains, forests, and nearby lakes.
Situated in the southeast of the state, Woodstock was founded in 1787 and has been an arts and crafts colony for a little over a century. As such, little studios, workshops and galleries are scattered about town, while live music and plays can be enjoyed at the Bearsville Theater.
In addition, it has some relaxing spas and retreats for guests to experience, and hosts numerous arts festivals, cultural events, and farmers markets during the year.
Made famous by Washington Irving’s legendary tale of the same name, Sleepy Hollow makes for a great quiet getaway and is just under an hour’s drive north of New York City. Due to the story’s infamous specter, the Headless Horseman, and the town’s atmospheric cemetery, it is regarded to be one of the most haunted places in the world.
This however doesn’t stop thousands of tourists descending on the town each year to see the historic sites related to the author’s short story, and its later film and TV adaptations. Aside from exploring the Sleepy Hollow Cemetery, you can also wander about the Old Dutch Church, and the various manors and estates that dot the area.
Besides taking tours around town, visitors can enjoy fishing or kayaking along the Hudson River. There’s also opportunities to go hiking, biking and horseback riding around the Rockefeller State Park Preserve.
Once a sleepy fishing town, Greenport is now known for its wonderful waterfront and wineries. Located near the end of the north fork of Long Island, the historic seaport has delicious seafood dishes, with plenty of beaches, views and water activities on offer.
Founded in 1682, Greenport has been an important port for the fishing, whaling and even oystering industries at various points in its past. Nowadays, its charming cottages are home to little local restaurants, art galleries, and antique shops, while sailboats bob peacefully about its marina.
Aside from simply enjoying the ambience or taking a scenic cruise around the surrounding waters, visitors can also head to any one of the forty or so vineyards and wineries that lie nearby.
Set along the shores of Cayuga Lake, the small town of Aurora is a picturesque place that is perfect for quiet getaways. Home to some beautiful old historic buildings, as well as idyllic inns and cozy BnBs, it can be reached in just an hour from either Rochester or Syracuse.
Mostly known for being home to the prestigious Wells College, which was originally for women only, the town is a treat to amble around. There are well-preserved historic homes and college buildings wherever you look. Although students make up most of its population, there is a lovely small town look and feel about the place.
In addition to snapping photos of its quaint center, visitors can enjoy splendid scenery and outdoor activities in Long Point State Park, or sample fine wines along the Cayuga Lake Wine Trail.
Nestled amidst the stupendous scenery and nature of the Adirondack mountains, the small town of Saranac Lake really is as picture-perfect as they come. A popular place to visit, it’s located alongside the reflective waters of Lake Flower, with wonderful woods and waterways lying all around it.
Founded in 1819, the small community has long drawn visitors to its shores, first due to its clear and restorative mountain air, and later for its excellent outdoor activities and festive Winter Carnival. Nowadays its charming old ‘cure cottages’ make for a pleasant place to stay as you visit sites, such as the Robert Louis Stevenson Memorial Cottage and Saranac Laboratory Museum.
Aside from ambling along the lakeside, you can also enjoy fantastic watersports or stop by its ample art galleries and historic sights. One of the best times to visit is during the winter carnival when all kinds of snow-related races, concerts, and celebrations take place.
Another of the most scenic settlements in the Finger Lakes region is the lakeside town of Skaneateles. Aptly meaning ‘Long Beautiful Lake’ in Iroquois, it lies at the northern end of the sparkling Skaneateles Lake and offers up the perfect mix of history, culture, and nature.
Home to well-preserved historic buildings, its tiny town center is a delight to wander around with unique boutiques, small art galleries, and local restaurants. Besides basking in breathtaking views from its two waterfront parks, you can venture out along the pier, take boat rides around the lake or enjoy superb watersports during the sunny summer months.
In addition, it also hosts a number of fabulous events, with the Skaneateles music festival, Antique and Classic Boat Show, and Dickens Christmas festival being the pick of the lot.
The largest and liveliest town in the Finger Lakes, Ithaca is home to both Ivy League Cornell University and prestigious Ithaca College. As such, it has a youthful feel, as well as thriving arts, culture, and nightlife scenes.
While its college campuses are home to some fantastic museums and historic buildings, downtown is packed with bookshops, restaurants, and a handful of great theaters. Besides boasting some of the most diverse dining and drinking options in the area, it also has countless wineries to visit nearby.
One of the town’s main draws, though, is its scenic setting at the southern tip of Cayuga Lake—there are over 150 waterfalls you can find in the nearby gorges, forests, and state parks.
Mostly known for being home to the National Baseball Hall of Fame and Museum, Cooperstown has much more going for it. Lying at the southern end of Otsego Lake, it has a wealth of outdoor activities and fine views for guests to enjoy, along with attractive architecture and interesting historic sites.
Established in 1786, the peaceful and picturesque town has a delightful historic district to explore that contains hundreds of well-preserved residences, businesses, and monuments. Besides the Hall of Fame, there is the excellent Farmers’ Museum and numerous art galleries, while brilliant performances are held each summer for the Glimmerglass Opera Festival.
Due to its stunning setting, Cooperstown has long attracted writers and artists. Its pristine nature and lake also offer everything from hiking and biking to swimming, fishing, and boating.
Tucked away amidst the Adirondack Mountains, the year-round resort town of Lake Placid has long been a popular place to visit, and it is easy to see why. As well as its stupendous scenery, landscapes and nature, it boasts an incredible array of outdoor activities, and even hosted the 1932 and 1980 Winter Olympics.
While synonymous with snow sports because of its proximity to the mountains, the town also has some great hiking and mountain biking to enjoy in the summer months. In addition, its nearby lakes and waterways offer splendid swimming and kayaking, with ice-skating and tobogganing to be had when their waters freeze over in the winter.
In addition to elite-level skiing and snowboarding, the small town has a charming centre to explore with lovely views over the surrounding lakes, forests, and mountains.
Just over an hour’s drive or train ride from New York City, the quaint town of Cold Spring is a very popular weekend getaway. Set in the scenic Hudson Highlands, alongside the river of the same name, it has a very attractive historic center with outstanding outdoor activities on offer.
Founded in 1846, its historic heart contains hundreds of nineteenth-century buildings with mansions and monuments lying next to churches and museums. Besides taking in its scenic streetscapes, you can also stop by its countless cozy cafes, unique boutiques, and restaurants.
From Cold Spring you can easily explore the nearby valleys and forests of the highlands, or enjoy fishing, swimming, and kayaking along the Hudson River.